Transgender and gender questioning people represent a unique group of clients who present specific challenges for psychotherapy. These clients experience a wide range of issues, some are gender specific while other issues are common among the wider population. This qualitative research paper explores the experiences of Irish psychotherapists working with transgender clients. It examines the subjective experience of three participant therapists and endeavours to make sense of the phenomenology that emerges from semi structured interviews. The phenomenological analysis of the data collected, results in three salient themes emerging. These themes are: (i) The therapist’s identification with transgender clients, (ii) The maternal/paternal countertransference and (iii) The symptom of confusion in the work with transgender clients. Strong identification with transgender people seems to act as a catalyst for psychotherapists to engage in this specific type of work. Their maternal/paternal countertransference effects the therapeutic approach and style of alliance they adopt. The symptom of confusion within the therapeutic space, reflects the client’s, the therapist’s and wider society’s confusion around transgenderism’s place within a binary culture.